You move from simpler hypotheses to more complex hypotheses for the same reason that you count from small numbers to big numbers.

Try imagining what counting the natural numbers "in the opposite order" would look like.

Of course, you can have large wiggles. For example, you might alternate jumping up to the next power of two and counting backwards. But using different representations for hypotheses leads to the same sort of wiggles in Occam's Razor.